Methanesulfonic Acid → 2-(6-chloro-1H-benzo[d]imidazol-1-yl)-8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purine

HRID 600418ノート

反応式

HRID 600418 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([CH3:24])[N:15]3[CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:11]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[N:10]=2)[C:5]([NH2:31])=[CH:4][CH:3]=1.[CH3:32]OC(OC)OC.CS(O)(=O)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:31]=[CH:32][N:8]([C:9]3[N:17]=[C:16]4[C:12]([N:13]=[C:14]([CH3:24])[N:15]4[CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:11]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[N:10]=3)[C:6]=2[CH:7]=1

参加物

5

反応物 3

HCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 670596105-chloro-N1-(8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purin-2-yl)benzene-1,2-diamine

生成物 1

HCID 461746802-(6-chloro-1H-benzo[d]imidazol-1-yl)-8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purine収率 22%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a vial containing crude 5-chloro-N1-(8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purin-2-yl)benzene-1,2-diamine (0.035 mmol) was added anhydrous methanol (2.5 mL), followed by anhydrous trimethylorthoformate (0.5 mL) and methane sulfonic acid (catalytic amount) and the reaction mixture was stirred under Ar at room temperature for 4 h (HPLC monitoring). Preparative HPLC purification, after evaporation of solvent and drying, provided the desired product (3.5 mg, 22% yield on two steps), as a yellow oil. TFA salt. 1H NMR (300 MHz, CD3OD+CDCl3) δ, ppm: 9.32 (s, 1H), 8.91 (br m, 4H), 8.79 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 4.76-4.72 (m, 1H), 4.32-4.29 (m, 2H), 3.72 (app t, J=11.7 Hz, 2H), 3.08-3.05 (m, 2H), 2.87 (s, 3H), 2.02 (br d, J=10.9 Hz, 2H); MS (EI) m/z 446.3 (MH)+.

後処理

  1. customPreparative HPLC purification
  2. customafter evaporation of solvent
  3. customdrying

出典と根拠

ORDレコード
ord-b6dcc75e83bd459cbad99996946e3e6c
出典データセット
uspto-grants-2011_03
特許番号
US07902187B2

反応ノート

読み込み中…